GILDERSLEEVE (Gilderslieve), HENRY, shipbuilder, ship’s captain, businessman, and justice of the peace; b. 8 Nov. 1785 in Gildersleeve (Portland), Conn., son of Philip Gildersleeve and Temperance Gibbs; m. 28 Jan. 1824 Sarah Finkle, and they had five sons, two of whom died in infancy, and three daughters; d. 1 Oct. 1851 in Kingston, Upper Canada.

Henry Gildersleeve came from a family of shipbuilders: both his father and his grandfather, Obadiah Gildersleeve, were ship-carpenters. Henry learned the trade in a shipyard in Gildersleeve before immigrating to Upper Canada in 1816. He obtained employment at Bath in the yard operated by Lucretia Finkle, widow of Henry Finkle, a loyalist and founder of the business. Gildersleeve helped in the construction of the Frontenac, which was built at the Finkle yard by Henry Teabout and James Chapman of Sackets Harbor, N.Y., where Gildersleeve is reputed to have worked as a shipwright about 1815. Launched in September 1816 by a group of merchants from Kingston and York (Toronto), the Frontenac was the first Canadian-built steamboat to ply Lake Ontario, beginning service between Kingston and Niagara (Niagara-on-the-Lake) on 5 June 1817. (An American steamboat, the Ontario, built at Sackets Harbor, began service on the lake early in 1817 [see Samuel Crane]. The first steamboat built in the Canadas, the Accommodation, had been constructed in Montreal in 1809 for John Molson*.)

Gildersleeve was master builder as well as part-owner of the second steamboat from the Finkle yard, the Charlotte, but was not a member of the committee which sponsored its construction. He acted as purser on this vessel while qualifying for his captain’s certificate, and in 1821 he became its captain. From 1818 to 1827 the Charlotte ran between Prescott, on the St Lawrence River, and Carrying Place, on the Bay of Quinte. The Sir James Kempt, which replaced the Charlotte on this run in 1828, was built under Gildersleeve’s supervision. He was a stockholder of the ship and served as its captain for many years before becoming its agent. His identification with these steamers and others that later plied the same route led to Gildersleeve’s designation by Edwin Ernest Horsey, a Kingston historian, as “the father of steam navigation on the Bay of Quinte and the upper St. Lawrence.”

Over the years Gildersleeve was involved both as a shareholder, in association with others (mainly Kingston businessmen), and sometimes as building superintendent, in the construction and operation of a succession of steamboats: William the Fourth (Gananoque, 1831), Commodore Barrie (Kingston, 1834), Henry Gildersleeve (Kingston, 1840), Prince of Wales (Kingston, 1841), and New Era (Kingston, 1848). Of these, the Prince of Wales plied the Bay of Quinte exclusively, while the others ran on that bay, on Lake Ontario, or on the St Lawrence. Gildersleeve also had interests in other steamboats. Along with Robert Drummond*, Donald Bethune*, and others he had been on the committee formed to build the John By, intended for the Rideau Canal but run instead on Lake Ontario. He became a shareholder in and later the agent for the Kingston, built by John G. Parker in 1833. In 1847 he purchased the City of Kingston, which had been built on Garden Island as the Prince Edward in 1841 by Dileno Dexter Calvin*, John Counter*, and others. Finally, Gildersleeve may have projected the construction of the Bay of Quinte, which was built under the direction of his son Overton Smith* in 1852.

Competition between steamboat operators became increasingly intense as the number of vessels multiplied. A bitter exchange of letters took place in the Kingston Chronicle in May 1830 between Gildersleeve and Archibald McDonell, whose ship Toronto had begun running on the Bay of Quinte. Gildersleeve also faced opposition there from Donald Bethune’s Britannia. To counteract the effects of competition, operators began coordinating their schedules and establishing joint undertakings. Gildersleeve, for instance, arranged for cooperation in the schedules of his Commodore Barrie and the American steamer Oswego in 1835. At various times, he chartered the Commodore Barrie, the Henry Gildersleeve, and the New Era to John Hamilton* of Kingston for service on his lines.

Gildersleeve had married a daughter of Henry and Lucretia Finkle in 1824, and by 1826 he and his wife had settled in Kingston, where he built a substantial stone house in 1825–26. He became a prominent citizen, known not solely as a shipbuilder but also as a man active in many business and community affairs. He was a stockholder of the Ottawa and Rideau Forwarding Company, which provided passenger and freight service between Kingston, Bytown (Ottawa), and Montreal via the Rideau Canal. With others, notably John Counter, he promoted and was an original stockholder of the Kingston Marine Railway Company, founded in 1836 and incorporated two years later. For many years Gildersleeve was a director and president of this firm, which built and repaired ships of all kinds at its marine railway and shipyard on the Kingston waterfront. He was a director and, later, treasurer of the Kingston Gas Light Company, and was a promoter of the Kingston Waterworks. As well, Gildersleeve was a founder and vice-president of the Kingston Provident and Savings Bank, president for several years of the Kingston Building Society, and vice-president of the Kingston Fire and Marine Insurance Company. As an investor, he held shares in both the Commercial Bank of the Midland District and the Bank of Upper Canada.

In response to early proposals for Upper Canadian railways, which threatened Kingston’s role as a trans-shipment centre, Gildersleeve and other enterprising businessmen conceived the idea of developing the city as the centre of a railway linking Toronto, Kingston, and (via Wolfe Island to the south of Kingston) Cape Vincent, N.Y., where it would connect with American railways. The Wolfe Island, Kingston and Toronto Rail-road Company was incorporated in 1846 but the railway was never built. An attempt to revive the plan, with the added feature of a canal across Wolfe Island, led to the incorporation in 1851 of the Wolfe Island Rail-way and Canal Company, of which Gildersleeve was named a director. He did not live to see the failure of this project, for he died in October of that year.

Gildersleeve participated in various other aspects of life in Kingston. He sat on the grand jury for the Midland District Assizes for several years and became a magistrate in 1842. The previous year he had served on the committee set up by the local board of trade to assess available accommodation for the use of the Canadian government after its scheduled move to Kingston. In religion he was an active member of St George’s Church (Anglican).

In 1828 the Kingston Chronicle described Gildersleeve as “well known for the urbanity of his manners.” A benevolent man, of strong character and firm integrity, he was above all a shrewd and far-sighted businessman and an enterprising pioneer in shipbuilding in Upper Canada. At his death he left a large estate, consisting of steamboats, real estate, and cash, to his son Overton Smith. Another son, Charles Fuller, and a grandson, Henry Herchmer Gildersleeve, gained prominence as managers of major shipping firms on the Great Lakes and the St Lawrence.

Ruth McKenzie